Waukesha Vacation Packages 2025/2026 from $517

Waukesha flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Cambria Hotel Milwaukee Downtown

Westown

$517

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Hilton Milwaukee

Westown

Save 100% on your flight

$691

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This luxury hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a garden are also offered.

Saint Kate - The Arts Hotel

Downtown Milwaukee

Save 100% on your flight

$771

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$824

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Holiday Inn Express Milwaukee Downtown by IHG

Downtown Milwaukee

$721

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Top Waukesha hotels deals

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$131 total

Oct 28 - Oct 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.

Pool

Hot Tub

Potawatomi Hotel & Casino

1611 West Canal Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$171 total

Oct 27 - Oct 28

Total with taxes and fees

A casino, 7 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking. Free self parking, a 24-hour business center, and a coffee shop are also offered.

Parking included

Free WiFi

Sonesta Milwaukee West Wauwatosa

10499 W Innovation Dr, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$102 total

Oct 30 - Oct 31

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Pool

Pet friendly

Holiday Inn Express Milwaukee-West Medical Center by IHG

11111 W North Ave, Milwaukee, WI

Free Cancellation

$98 nightly

$114 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling for business? Take advantage of the business center, laundry service, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Breakfast included

Pet friendly

Hyatt Regency Milwaukee

333 W Kilbourn Ave, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$110 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Pet friendly

Free WiFi

Sonesta Select Milwaukee Brookfield

16865 W Bluemound Rd, Brookfield, WI

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$87 total

Nov 13 - Nov 14

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

Pool

Pet friendly

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee Art Museum

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Frequently asked questions

How much are vacation packages to Waukesha?

$517 is all you'll need for an unforgettable vacation in Waukesha. Bundle your hotel and flights into a vacation package with Travelocity and see your savings start to pile up. With prices this good, it's never been easier to travel!

How long should my Waukesha vacation be?

If you're looking for some guidance, most visitors spend around 2 nights in Waukesha. But to uncover the true essence of this place, stay a few extra days. You'll be able to get to more attractions and really experience the local vibe.

Where can I get the best vacation package deals for Waukesha?

Head straight to Travelocity. With access to 400 air carriers and 1,000,000 worldwide properties, selecting the perfect Waukesha package deal couldn't be simpler.

Why should I book my Waukesha vacation package via Travelocity?

Whether you're on the hunt for the ultimate unplugged vacation or you crave the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need them.

Will I save money on my Waukesha car rental if I book it with a hotel or flight?

Certainly — combine your car, hotel and flight into a Waukesha vacation package and you can save tons. With so much to discover in Waukesha, that set of wheels will more than come in handy. Once you're in the driver's seat, turn up the stereo and cruise toward Wrigley Field, a top sight about 80 mi from Waukesha.

Which airport is best for Waukesha?

General Mitchell Intl. Airport (MKE), 17 mi east of the city center, is where many people begin their Waukesha adventures. But it's possible that Dane County Regional Airport (MSN) (55 mi away from central Waukesha) could suit you better.

What is there to do in Waukesha?

Waukesha is teeming with places to explore, including Center Court Sports Complex and Infinity Fields Baseball Park. These well-known attractions top most travelers' travel itineraries.

Where should I stay when visiting Waukesha?

Many people choose to check in to the Tru By Hilton Milwaukee Brookfield. It's sure to be a great base for your Waukesha escape.